(S)-2-tert-butoxycarbonylamino-6-diazo-5-oxohexanoic acid tert-butyl ester

Base Information

Chemical Name:(S)-2-tert-butoxycarbonylamino-6-diazo-5-oxohexanoic acid tert-butyl ester
CAS No.:208520-00-7
Molecular Formula:C₁₅H₂₅N₃O₅
Molecular Weight:327.381
Hs Code.:

Synonyms:(S)-2-tert-butoxycarbonylamino-6-diazo-5-oxohexanoic acid tert-butyl ester

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Chemical Property of (S)-2-tert-butoxycarbonylamino-6-diazo-5-oxohexanoic acid tert-butyl ester

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Technology Process of (S)-2-tert-butoxycarbonylamino-6-diazo-5-oxohexanoic acid tert-butyl ester

There total 1 articles about (S)-2-tert-butoxycarbonylamino-6-diazo-5-oxohexanoic acid tert-butyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.0%

: 91229-91-3
tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate

: 18107-18-1
diazomethyl-trimethyl-silane

: 208520-00-7
(S)-2-tert-butoxycarbonylamino-6-diazo-5-oxohexanoic acid tert-butyl ester

Guidance literature:: With n-butyllithium; In tetrahydrofuran; hexane; at -105 - -100 ℃; for 0.166667h;

Reference yield:

: 208520-00-7
(S)-2-tert-butoxycarbonylamino-6-diazo-5-oxohexanoic acid tert-butyl ester

: 504-91-6,1190-94-9,3506-26-1,6000-08-4,18899-29-1,18899-30-4,18899-31-5,52153-41-0,78088-29-6,28902-93-4
(5R)-5-hydroxy-L-lysine

Guidance literature:: Multi-step reaction with 7 steps

1: 5.76 g / aq. HBr / diethyl ether / 0.42 h / -20 °C

2: 77 percent / NaBH₄ / methanol / 3 h / 0 - 20 °C

3: 28 percent / 1,3-dicyclohexyl carbodiimide; 4-dimethylaminopyridine / CH₂Cl₂ / 16 h / 20 °C

4: NaN₃ / dimethylformamide / 6 h / 80 °C

5: LiOH / tetrahydrofuran; H₂O / 4 h / 20 °C

6: H₂ / Pd/C / ethanol / 4.5 h

7: TFA / H₂O / 2 h / 20 °C

With dmap; lithium hydroxide; sodium tetrahydroborate; sodium azide; hydrogen bromide; hydrogen; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 1: Substitution / 2: Reduction / 3: Esterification / 4: Substitution / 5: Hydrolysis / 6: Catalytic hydrogenation / 7: Hydrolysis;
DOI:10.1016/S0040-4020(98)01023-0

Reference yield:

: 208520-00-7
(S)-2-tert-butoxycarbonylamino-6-diazo-5-oxohexanoic acid tert-butyl ester

: 6-bromo-2-tert-butoxycarbonylamino-5-(3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-hexanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 5.76 g / aq. HBr / diethyl ether / 0.42 h / -20 °C

2: 77 percent / NaBH₄ / methanol / 3 h / 0 - 20 °C

3: 81 percent / 1,3-dicyclohexyl carbodiimide / CH₂Cl₂

With sodium tetrahydroborate; hydrogen bromide; dicyclohexyl-carbodiimide; In methanol; diethyl ether; dichloromethane; 1: Substitution / 2: Reduction / 3: Esterification;
DOI:10.1016/S0040-4020(98)01023-0